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Here are this week’s travel contests. There are tons of great sweepstakes to win this week!

You can win trips such as a Sandals resort stay; a trip to the F1 race in Las Vegas, Nevada; the Greek Islands; Seattle, Washington; Tokyo, Japan; Breckenridge, Colorado; an RV; Australia; Thailand; Madrid, Spain; Walt Disney World in Orlando, Florida; Madeira, Portugal; South Africa; England and France; Montego Bay, Jamaica; Hawaii; Italy; Alaska; Petaluma, California; Key West, Florida; France; Puerto Rico; the Bahamas; Quebec, Canada; an Alaskan cruise; and more.

Good luck! Be sure to subscribe to my weekly newsletter so you don’t miss any sweepstakes, and please share this post with friends who might take you along if they win!

Do you find my weekly travel contest emails useful & have upcoming travel that you need to book? Use my travel resources page to make your bookings! There’s no cost to you, and you’ll be supporting my site. Thanks!

Win a Sandals resort stay (new for Q3, previous entrants can enter again!)

  • There will be one (1) Grand Prize awarded following the conclusion of the Promotion Period. The Grand Prize Winner (“Winner”), upon confirmation of eligibility, will receive a 4-day/3-night “All-Inclusive” vacation package for two (2) adults (for travel a year from the printed prize certificate) to a Sandals Resort or Beaches Resort of Winner’s choice (excluding Sandals Royal Plantation, Sandals Barbados, Sandals LaSource and Sandals Emerald Bay) (“Prize” or “Grand Prize”). The Prize includes one room (double occupancy) Deluxe Suite and “All-Inclusive” amenities offered at the selected or designated resort, including local airport transfers, unlimited food and beverages (including premium brand drinks), an array of land and water sport activities (scuba diving for certified divers), daily and nightly entertainment, Wi-Fi in all rooms and public areas, resort gratuities and resort taxes. “All-Inclusive” amenities are subject to change and are to be determined by Sponsor in its sole discretion. The Grand Prize will be issued in the form of a prize certificate redeemable by filling in requested information and mailing back to the address indicated. The Grand Prize Winner must call the given telephone extension on the prize letter to arrange trip details. Note: Airfare is not included
  • open and offered only to legal residents of the USA and Canada, who are at least eighteen (18) years of age
  • Enter by September 30, 2025

Win a trip to Las Vegas, Nevada

  • An invitation to the Las Vegas Grand Prix with two tickets to the Mercedes-AMG PETRONAS F1 Team Vegas Club for Thursday November 20 through Saturday November 22.
    Opportunity for our winner to experience a Hot Lap around the track in a Mercedes- AMG GTR
    Opportunity to meet Mercedes-AMG PETRONAS F1 Team Personnel
    A 4-night stay from November 19 to November 23 at The Cosmopolitan of Las Vegas
    Round-trip air transportation from US or Canadian airports to Las Vegas, NV
  • Enter by October 26, 2025

Win a trip to the Greek Islands (no donation required)

  • 7 Night Idyllic Aegean Cruise around Eastern Mediterranean for Two including Santorini and Mykonos
  • Roundtrip flights for two to/from Athens, Greece booked through OneAir.ai, up to $3,000
    Journey Dream Suite
    Port charges/gratuities
    Complimentary dining
    Premium drinks package
    Complimentary $160 shore excursion discount
    1hr wi-fi
    25% speciality dining discount
    1 Pre Cruise Night & 1 Post Cruise Night in Athens Capital Center Hotel MGallery Collection.
  • open only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by September 30, 2025

Win a trip to Seattle, Washington (no donation required)

  • Flights: Roundtrip flights from select major international airports in mainland USA (excluding Alaska and Hawaii) to Seattle, Washington
  • Rental Car: For 3 days, including GPS hire and $100 fuel allowance (pick up/drop off from Seattle)
  • Accommodation: 2 nights’ luxury cottage accommodation nearby to Seattle, Washington
  • Private Horseback Riding Lesson: (1 hour) Includes professional instructor and all equipment
  • open only to legal residents of the United States of America who are 18 years old or older and all United States Territories
  • Enter by September 30, 2025

Win a trip to Tokyo, Japan (no donation required)

  • $2,500 towards round-trip airfare for two
  • $1,000 towards 4-night hotel stay near Tokyo Disneyland
  • $1,500 towards two 2-day passes to Tokyo Disneyland and DisneySea and exclusive Disney merchandise
  • only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by October 19, 2025

Win a trip to Breckenridge, Colorado

  • 12 Monthly Winners will receive:
  • Four nights at the Grand Colorado on Peak 8 in a one-bedroom residence.
    $1,000 cash to spend on travel, souvenirs and more!
    $150 resort credit that can be used on food, drinks and spa treatments.
  • Must be 21 years of age or older at time of entry to be eligible for this contest and a legal resident of the fifty United States and Washington, D.C. 
  • Enter by November 30, 2025

Win an RV

  • There are four (4) Grand Prize RV Winners (up to a $20,000 credit towards each). The $20,000 prize is a credit towards an RV purchase at Camping World/affiliated locations. The Prize Winner may use up to $20,000 on the purchase of an RV of their choice at their nearest Camping World. The Prize Winner will be responsible for the financing of the remaining balance of the RV if the cost of the RV exceeds $20,000. Any remaining balance of the credit will be forfeited and cannot be redeemed for cash
  • open to all legal residents of the 48 contiguous United States and the District of Columbia (excluding Alaska, Hawaii, and Puerto Rico), who are eighteen (18) years of age or older
  • Enter by December 31, 2025

Win a trip to Australia (no donation required)

  • There will be 1 Prize awarded (“Prize” and/or “Prizes”), consisting of all the following:
  • Up to $4000 towards Roundtrip airfare to Australia and local transportation in Australia
    Up to $1000 towards Hotel Accommodations
    2 Tickets to see Ed Sheeran in Docklands – Melbourne, Australia on February 27, 2026
  • open only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by January 23, 2026

Win a trip to Thailand (no donation required)

  • The Pavilions Hotel & Resorts (Phuket, Thailand) Prize Package; Est. Retail Value: $10,000
    Includes 7 Night Resort Stay for two (2) in an Ocean Villa room category, daily massage, round trip transfers from the airport, breakfast included, and a Thai cooking class
    No person under the age of 18 shall be permitted to make a reservation.
    The responsibility of possessing a full-valid passport and/or visa where necessary is the responsibility of each individual traveling.
    Travel valid from April 1, 2026, to March 31, 2027
    Blackout dates apply from December 24, 2026, to January 10, 2027.
    $1,500 towards Airfare; Cash/Retail Value: $1,500
  • open only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by March 1, 2026

Win a trip to Madrid, Spain (no donation required)

  • There will be 1 Prize awarded (“Prize” and/or “Prizes”), consisting of all the following:
  • up to $3000 towards Roundtrip airfare and transportation
    Up to $1000 towards Hotel Accommodations
    2 Tickets to see Bad Bunny in Madrid, Spain on June 15, 2026
  • open only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by May 11, 2026

Win a trip to Walt Disney World

  • One lucky winner and up to seven guests will enjoy a Walt Disney World® Resort vacation that includes:
  • 6-night stay at Disney’s Riviera Resort in a spacious 2-Bedroom Villa
    7-day Theme Park Tickets, with Park Hopper® Option
    Special access to Member Lounges in Magic Kingdom® Park and EPCOT®
    Pending winner travel dates, entry to an after hours Member Event
    Round-trip coach airfare and ground transportation
  • Open only to legal residents of the 50 United States (D.C.), 18 years of age and older
  • Enter by September 24, 2025

Win a tour of Madeira, Portugal (airfare not included)

  • Enjoy a clifftop stroll of the Sao Lourenco Peninsula
  • Walk along the unique irrigation channels of the Levado
  • Bask in the spectacular alpine views of the Balcony Walk
  • Explore beautiful gardens and a colourful farmers market
  • Open worldwide, 18+
  • Enter by September 30, 2025

Win a trip to South Africa

  • Return Economy Flights for two to Cape Town.
    3 nights in the Marriott Hotel, Crystal Towers.
    Choice of Stellenbosch Wineries or Table Mountain tour in South Africa
    A 2-day safari including 2 nights at Inverdoorn Private Safari Lodge.
    A Cheetah Educational Tour & Cheetah run experience.
    VIP travel management.
  • open to any person residing in Australia, New Zealand, the United Kingdom, Europe, the United States of America (excluding New York State & Florida), Canada (excluding the Province of Quebec), South America and South Africa, aged 18 years and over
  • Enter by September 30, 2025

Win a trip to England and France

  • Grand Prize includes: An 8-day Paris & the Heart of Normandy river voyage; 3-night land extension program visiting Oxford & Highclere Castle; roundtrip international Business Class flights for two.
  • Open only to persons twenty-one (21) years of age or older who are permanent legal residents of the fifty (50) United States, the District of Columbia or Canada, or are United States or Canadian citizens with a permanent United States or Canadian address and currently residing on an overseas United States or Canadian military installation (collectively an “Entrant”) (excluding the Province of Quebec, Puerto Rico, and all other U.S. territories and possessions)
  • Enter by September 30, 2025

Win a trip to Montego Bay, Jamaica

  • Win a 4-night all-inclusive stay for two at RIU Palace Jamaica compliments of Apple Vacations. Included in the prize are flights for two people from nearest Flight Gateway to MB, Montego Bay. Travel by October 1, 2026 (no extensions allowed) pending availability. See rules of the sweepstakes. Other prizes include $500 in luggage compliments of Steamline Luggage and a Via Citrus Tree valued at $70.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by September 30, 2025

Win a trip to Hawaii

  • One (1) Grand Prize will be awarded. The Grand Prize is a trip for winner and one (1) guest to stay at Sensei Lanai, Four Seasons Resort in Lanai City, Hawaii, subject to availability. Prize ARV: up to $10,000. Odds of winning depend on the total number of eligible drawing tickets received during the Sweepstakes Period. Grand Prize consists of all elements below (total ARV for all elements must not exceed $10,000):
    (a) round trip, coach class air transportation for winner and guest from a major commercial airport located within the United States near winner’s place of residence to winner’s destination as described above. If winner resides in Hawaii, Sponsor reserves the right in its sole discretion to substitute ground or ferry transportation for air transportation, where applicable.
  • (b) three (3) nights’ hotel accommodations (standard double-occupancy room, room and room tax only, as selected in Sponsor’s sole discretion) for winner and guest.
  • (c) selected meals on property (at Sponsor’s sole discretion)
  • open to legal residents of, and physically residing in one of the 50 United States or the District of Columbia, age 18 or older
  • Enter by September 30, 2025

Win hotel stays in Italy (airfare not included)

  • Win a 2 night stay in both Venice and Rome in 4-Star Superior Hotels with Business class transfer on the Fast Train compliments of Your Custom Journey. Blackout dates include April 3-7, 2026, May 5-8, 2026 and September 2-12, 2026.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by September 30, 2025

Win an Alaskan cruise and camera equipment (airfare not included)

  • One (1) Sony Mirrorless Camera (Model #: ILCE-7RM5) (ERV: $3,899.99)
    One (1) Sony Lens (Model #: SEL70200GM2) (ERV: $2,799.99)
    One (1) Sony Lens (Model #: SEL2470GM2) (ERV: $2,299.99)
    One (1) Promotional Cruise Voucher for a Holland America Alaskan seven (7) day cruise for
    Grand Prize Winner and one (1) guest. Sailing must be completed by September 30, 2026.
    Excludes all July and August sailings onboard Eurodam, Westerdam and Koningsdam.
    Airfare and ground transportation are not included. Promotional Cruise Voucher is subject
    to additional terms including as set forth below. (ERV: $3,222.00)
  • open only to legal residents of the United States (excluding US territories) and Canada (excluding the Province of Québec)
  • who at the time of entry are at least twenty-one (21+) years of age
  • Enter by September 30, 2025

Win a trip to Petaluma, California

Win a trip to Key West, Florida

Do you have upcoming travel that you need to book? Use my travel resources page to make your bookings! There's no cost to you, and you'll be supporting my site. Thanks!

  • We want to send you and a guest to Mile 0 Fest in Key West to see artists like Stephen Wilson Jr., Randy Rogers Band, Shane Smith & The Saints, Casey Donahew, Kaitlin Butts and more!
  • Your ticket to paradise for you and a guest includes:
  • $1,000 towards travel to sunny Key West
    3-night stay at a participating hotel
    3-day music passes to Mile 0 Fest at the Truman Waterfront Amphitheater
    3-day chair rental for two
  • open to the legal residents of the US, 21+
  • Enter by September 30, 2025

Win a Scenic Paris, Normandy, and Loire Valley Trip (airfare not included)

  • Uncover France’s beauty with a 9-night self-drive vacation.
  • Tour Loire vineyards, Normandy’s historic coast, Rouen’s Gothic cathedral, Versailles, the Louvre, and the Eiffel Tower.
  • Inclusions:
  • 09 nights in superior hotels or similar
  • Daily breakfast
  • Car rental for 09 days (Renault Megane or similar)
  • -Pick-up/drop-off at Paris Airport
  • Unlimited mileage
  • Theft protection & collision damage waiver
  • Option to upgrade to automatic (extra fee)
  • All currently applicable taxes
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by October 1, 2025

Win a trip to Puerto Rico

  • 3 Nights at Casa Islena (accommodations for 2)
  • $500 AMEX Gift for Travel
  • $100 resort credit for poolside cocktails
  • 2 days of personal surf lessons for two
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by October 2, 2025

Win a Bahamas cruise (airfare not included)

  • The prize includes accommodations for up to four in one room on a 3-Night Bahamas Cruise in an inside, ocean view or balcony stateroom of up to $2,000 in value, selected by winner subject to availability on MSC Cruises’ MSC Seashore. Cruise departs and ends from Port Canaveral, with planned calls in Nassau Bahamas and Ocean Cay Marine Reserve. Departure dates are available from January 1, 2026 through June 30, 2026 and may be selected by prize winner dependent upon cabin availability at time of booking, not to exceed a cost of $2,000. Prize includes stateroom accommodations for up to four, onboard dining (with exception of specialty restaurants), onboard shows & entertainment and fitness center access. Prize does not include airfare, transfers, drink packages, shore excursions, onboard gratuities, Wifi, specialty restaurant dining, fitness classes, or upgrades.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories) 
  • Enter by October 3, 2025

Win a stay in Quebec, Canada (airfare not included)

  • ENTER FOR A CHANCE TO WIN A TRIP TO FAIRMONT LE MANOIR RICHELIEU in Quebec, Canada.
  • Your Prize includes:
  • 3-night stay for two in a Fairmont View room in Quebec, Canada.
    Breakfast for two daily.
    One hour Spa treatment for two.
    Daily resort experience fees.
    Welcome in-room amenity.
    Daily valet parking.
    $250 Amazon gift card compliments of Mode Mobile.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by October 3, 2025

Win an Alaskan cruise

  • One (1) Grand Prize winner will receive 500,000 AAdvantage® miles and up to a 7-night cruise for 2 to Alaska in a balcony stateroom on Norwegian Cruise Line
    Five (5) First Prize winners will receive 100,000 AAdvantage® miles
  • open only to legal residents residing in the 50 United States and D.C., 21 years of age or older
  • Enter by October 5, 2025

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

Which travel giveaway are you most excited about winning this week?

Why not share this post with your friends? If they win, maybe they’ll take you!

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Hi, I'm Jonathan, the traveler, writer, photographer, enthusiast, & terrible dancer of Everybody Hates A Tourist with decades of travel expertise. I've visited over 40 countries so far. Join me as I share my personal experiences finding the best food, craft beer, cocktails & spirits, wine, culture, & history around the world!

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